Never Underestimate the Power of Cheap Whiskey
by riotboi
Summary: Dean is left hurting after Bobby's death and Sam is unsure about how to comfort him. But there's one thing you can say for the Winchesters, they never back down from a challenge. Dean/Sam pairing. If that's not your cup of tea, by all means toddle along to another story and enjoy your day. M for language, sexuality, and alcohol/consent issues which might be triggering for some.
1. Chapter 1

**Never Underestimate the Power of Cheap Whiskey**

**Notes**: Obviously none of the character are mine.

**Warnings**: Geez, this should just come standard on everything I freaking write...BUT...lewd, crude, tastelessness up ahead. This first section is reasonably tame, but the second won't be, just a heads up. If you aren't into Wincest, sorry this story won't be for you, by all means go read something else and have a lovely day. If you wanna bitch and moan about how it's an awful pairing, could you just yell at the screen instead of typing it? I'm all for constructive criticism, but if that's your idea of constructive criticism then I pity anyone who comes to you for advice.

_I'll put more emphasis on this in the second installment, but we're dealing with a characterization of both Dean and Sam who have already entertained these thoughts of one another. They've both dealt with it in different ways, but the inclination is still there. I'd go into the backstory and all that goodness but then this would be a much longer fic, and we've all seen how well I do plodding through multi-chapter fics. (It doesn't get done, basically.)_

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More than anything Dean couldn't understand why the time was passing so slowly. He groaned, stiff, and shifted slightly so that the Impala's hood wasn't pressing into quite the same spots on his back. The cellphone's screen, blindingly bright in the dark night, had only advanced about a quarter of an hour since he last checked, which had only been five minutes after the previous check, and that only twenty after the one before...and so on and so forth. The short an long of it was, the night seemed endless. Just like the day had been and the next day would be.

Ever since Bobby had died he and Sam had sat in near total silence, time at a crawl. It made no difference whether Dean tried to distract himself or not, either way the days moved slower than sloths edging their way along tree branches. Did you know that it could take days for two sloths to have sex? Dean didn't need to know that, but when Sam, random factoid extraordinaire was your brother, you got to save little things like that for rainy days.

The wilderness surrounding the cabin they were sheltering in was vast and very little light pollution dampened the overwhelming, pressing darkness of night. Dean had driven the Impala out to a clearing off the road a few miles out with enough cheap liquor to black out Superman, it was a ritual he had gotten into two days after they had left the hospital. The first night had been reserved for a proper hunter's burial for Bobby, they chopped the wood for the pyre all day and at sundown said their last goodbyes. Dean wondered whether it would be good enough, Bobby had at least a couple of possessions that Dean could imagine a spirit attaching itself to upon death, but only time would tell.

There was a difference tonight than there had been for the last week though. The blackness, save millions of stars blanketing the sky, had stripped him down to purely auditory and physical input. Warm whiskey. Chilly still night air pressing the air out of his lungs. The Impala's hood warm under his back, engine not fully cooled from the drive out. Cicadas and crickets crying out their unearthly unbroken whine. All the same as before. But this time there was a warm presence next to him as well.

Sam.

Sam had pestered him all day to bring him along, using every ploy in his arsenal which, considering he'd had a long time to learn every single issue that raised Dean's hackles and pricked his conscience, was extensive. Regardless of how reluctant Dean had been, he had to admit that Sam's presence was comforting.

"Look," Sam glanced over, barely able to make out Dean's outstretched arm pointing into the night sky. "That constellation is Boötes. Apparently it's in the running for 'oldest constellation ever'. Pretty impressive claim, huh?"

"I didn't know you knew about constellations," Sam said with slight consternation as he tried to search out the proper arrangement of stars above.

"You think you got all the brains in the family?" Dean huffed out what could loosely be called a laugh. His first since... "I do read, ya know."

Sam snorted, sounding unimpressed. But inside he was glad to be talking like normal. His favorite moments were like this, with Dean, sitting on the Impala listening to his brother jabber on about something he hadn't expected him to know about. Dean was always surprising him like that. The ridiculous playboy act and the general family expectation for Sam to the smart one always and forever were incongruous with this quiet, confidently knowledgeable Dean. It made, for just a second, the last week, Hell the last few years, fall away and Sam hoped the mood wouldn't just slip away.

"Where is it?" Sam asked quietly, sliding over so his shoulder pushed up against Dean's.

"See, you can see him if you spot Ursa Major and Minor," Dean continued circling his finger lazily towards the sky.

The older brother continued to babble on about constellations, picking out their shapes with his hand, still holding the bottle of whiskey, and describing their various stories. Sam just leaned back and listened, giving appropriate noises of encouragement periodically, just to make sure Dean wouldn't stop. He was paying more attention to Dean though than the stars, beautiful as they were. His brother's familiar smell, leather and cheap soap and cheaper alcohol, overtook his senses. It was the smell of home, comforting and right. Throughout the years the way Dean smelled had barely changed and nothing else could calm Sam as much as simply being near his brother and letting that scent surround him.

His older brother's eyes shone bright with alcohol and momentary happiness as he stared up at the stars, still lost in the ancient stories. Dean's profile was sharp against the darkness and Sam couldn't break his

gaze. Why couldn't they stay this way always? The way they were meant to be.

Sam didn't notice when Dean stopped talking or when he lowered his hand from the sky. But he did notice when Dean silently turned his head to stare straight into Sam's eyes. Even in the dim light the stars provided, Dean's eyes flashed green and captivating. There was too much behind the look to unpack it at one glance, Sam was sure he saw the sadness that had overtaken their lives last week, and certainly a haze of whiskey. There was deep seated anger and resolution there too, as there always was, and the fierce protective urge Dean had directed towards his younger brother their entire lives. But there was something more, Sam though, flickering through the green, if he could only catch up with it and dissect it.

"I feel worse," Dean rasped quietly, "even worse than when Dad died. Bobby...he was...he was more than...fuck, he was the closest thing to a loving parent..."

"Yeah. I kind of feel like an asshole, but I feel like this is what it should have felt like when Dad died."

"Exactly. But Bobby deserves just as much as he does," Dean broke off, still unused to saying anything truly against their father.

"Maybe...maybe it's because when Dad died we still had people. Shit, just look around us. Bobby was the last family we had."

"We're actually fucking alone this time, aren't we, Sam?"

Dean looked so desperate Sam's throat knotted up. He never knew what to do the few times Dean actually let him see the pain he was truly in underneath it all. Dean was always the one to take care of things, to take care of Sam, he hadn't learned how to return the favor. Shit, what should he do? What would he do for someone else?

Gut lurching with nerves that Dean would push him away, get cold and angry again, or even drive off and leave him alone in the woods all night, Sam reached over and placed his hand softly on Dean's cheek.

His brother flinched and a flash of confusion crossed his handsome features, but thankfully he didn't run screaming.

"We'll be ok, Dean," Sam said more confidently than he felt. "Just the two of us, we can take care of each other just fine. We'll miss the Hell out of Bobby and that's ok, but we...we can get by."

He leaned over and placed a chaste kiss on his brother's lips and then settled back a comfortable distance, trying not to show that he was bracing for the shit storm he fully expected. Dean's lips were just as he had remembered from when Dean used to tuck them into whatever cheap motel twin bed they called home each night, warm and soft as sin. It had been a comforting gesture then, maybe it still could be now?

"Sam," Dean's voice cracked, eyes still locked on his little brother. His heart had jumped at Sam's kiss, the first they'd shared since Dad had started yelling that it wasn't right for two boys to do that at their age, when Dean was about thirteen. So many years and it still felt like home.

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**Aw aren't they just so adorbs when they're sad. Mansobs all around. I like it when we get to see the adept, unexpectedly nerdy side of Dean. I feel like it's often overlooked in portrayals of his character. Exciting stuff in the next chapter and I'll warn you, it's pretty glurgy, but what do you expect when it's all about comfort?**


	2. Chapter 2

**Never Underestimate the Power of Cheap Whiskey, Part 2**

**Notes**: Yep, they still aren't my characters. (My characters are much more well rounded and far less misogynistic. Just kidding! Well, about the well rounded part...)

**Warnings**: Okie dokie folks...there's gonna be a lot under this subheading. First, I feel like a lot of these fics are written by people who are actually straight/have no idea how any non p in v sex works. I've glossed over a fair bit just to make the story spicy, but I'm a stickler for cleanliness and consent. You will see a wee bit more emphasis on safe sex in this than you might be used to. You will also see a nod to good consent culture (which is then duly ignored because otherwise there wouldn't be a story and writing this without Dean drinking would be completely out of character). If alcohol based consent issues are triggering for you, this might be the time to turn back. Now, if you're still hung up on the incest bit...well, I don't know why you're reading this in the first place to be quite honest. Go find something else that makes you happy and read that instead.

_Also, this is a super glurgy ( I believe the regular internet word is shmoopy) story. It's sickly sweet which was both unintentional and a happy discovery (at least for yours truly). I've got enough angsty writing elsewhere and I figure these boys could use some happy times._

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Dean wouldn't have been able to adequately describe the thought processes that led to him kissing Sam back. What combination of mutual reliance, heartbreaking loss, and bad whiskey could have spurred him on, it was after all, a fairly usual combo for him and yet the outcome was decidedly less so. But he'd leave the answer up to someone smarter than himself, Sam maybe, because he was too damn focused on never letting Sam's lips leave his for the rest of their goddamn lives.

So much more so than any girl he'd ever made out with in the back seat of the Impala or boy he'd thrown up against the sticky back wall of a bar, Sam's lips seemed to fit against his like they were made for him to kiss. The fact that Sam was heartily kissing him back just made the deal sweeter. It would have been damn awkward otherwise and Dean was not in a place to deal with emotional drama right now. But whiskey and a warm familiar body and comfort, that he could definitely use some more of right this second, thank you very much.

Sam had been overwhelmed, pleasantly so, but still definitely overwhelmed when Dean broke the staring contest they'd begun after the first kiss. His older brother, shorter though he may be, was still fully capable of throwing Sam around and he'd knocked the wind out of Sam as he was flipped roughly over onto his back. Dean seemed to want to be in control of the situation. Hell, Sam had seen Dean with enough people to know that he was always in control of the situation, sharing rooms their entire lives had definitely been more than adequate to teach Sam a thing or two about what Dean liked. And maybe, just possibly in the back of his mind, Sam had wondered about what it would be like to be one of those people.

Their mouths were hard against each other, the pain and need welling up inside each of them seemed to come bursting out at the juncture of their lips. Breaths came like sobs as the brothers pressed in tighter, closer, wished they could crawl inside one another and stay there forever, thinking there was just a chance that that might actually feel like peace.

Rough hands pushing up under Sam's shirt, latching onto his hips heavy and hot, were the first indication Sam had that this might lead to something more. Dean's hips bucking against his were the second.

"Dean," Sam reached up and placed one large hand on either side of his brother's face, needing affirmation, needing just a word that they were on the same page. Comforting his brother was one thing, taking advantage of his drunken, grief ridden brother was another and a cold knot in Sam's stomach warned him he might be leaning more towards the latter. "Is-is this something you want, Dean?"

Dean's eyes were wild with desperation and lust, his pupils expanded so there was only a tiny hoop of green visible around the black. He panted and pushed, trying to get back to Sam's mouth. "No talking Sammy, come on," he breathed.

"No, Dean," Sam was going to hate himself for stopping this later, but he'd probably hate himself more if he didn't continue without Dean's consent although, with him as drunk as he was, that would be a major grey area no matter what he said. "You're drunk as hell and you're not thinking clearly. Is this what you want?"

The sharp note in Sam's voice seemed to shake Dean just a little. The wildness subsided a little, and he focused enough to catch Sam's gaze and hold it steadily.

"Sam, man, we're all we have left. I need you. I've always needed you." The confession was difficult and embarrassing as hell; Dean was very glad at that moment that he was drunk because he wasn't sure he'd have been able to say it otherwise.

There was a softness when Sam pulled him down into a kiss this time. A few kisses, warm and gentle enough to melt him like butter before Sam pulled away again. Dean keened quietly as his brother's lips pulled away, _why couldn't Sam just stop thinking for once?_

"I know, Dean, trust me I know. But this," his eyes swept up and down between their bodies tangled up atop the car, "Is this what you're going to want tomorrow? Dean, I just couldn't take it if..."

"Are you asking me if I'm going to freak out tomorrow because I fucked you tonight?" Dean pushed his hips in just a little tighter as he finished speaking and he could feel Sam shiver deliciously underneath.

"Yeah," the reply was breathless, "pretty much."

The only reply he received was Dean's sudden absence. His brother slid off him onto the ground and walked towards the passenger side of the car. Every place Dean had been touching was now hit with the chill night air and Sam cringed. _Fuck_, he thought as he collapsed heavily down onto the hood of the Impala, now he'd done it. Crossed that line he swore to himself he'd never cross and now he'd be losing the only family he had left. _There was no way Dean would forgive him for..._

The door jolted the car as it swung shut and Sam heard Dean's boots crunching through the autumn leaves towards him again. _Here we go_, Sam thought, _time for a fight_. But as he was just about to push himself upright, several wrapped condoms, a latex glove, and an on-the-go packet of lube landed lightly on his lap.

A very smug looking Dean crawled his way up between Sam's legs again. "Didn't think I'd make you do it with just spit did you?"

He positively beamed at Sam, radiating a level of cockiness only Dean could ever pull off.

"Dean, where...?"

"Dude, do you ever look in the glove compartment? I'm always prepared."

His hands were unbuckling Sam's belt before he even had a chance to respond. Jeans, boxers, and all followed shortly thereafter and Sam fervently wished he was drunk enough to ignore the cold, like his brother obviously was.

A hot mouth on his inner thigh silenced the extreme confusion/bitching about the cold monologue running through his brain though. In fact it may have stopped his brain functioning altogether. Sam would have to check back with you on that when his brother was no longer nibbling his way up towards his increasingly needy cock.

Dean hiked Sam's long legs up over his shoulders, face buried tight between, lapping and sucking away at all of the sensitive skin he could find. Everywhere except...it was Sam's turn to whine, desperate to feel that deliciously warm tongue on him. He heard an exceptionally self satisfied chuckled from between his legs before Dean raised his head enough to tease, "Well, Sammy, what is it you want?"

"Want," Sam gasped as Dean's head lowered back down and started sucking out a hickey on the soft skin right next to his hip bone. "Want you to..."

"To?" More chuckles as Dean used the leverage of Sam's legs on his shoulders to hoist his younger brother up to where his hands could slip underneath and grab his ass.

"Dammit, Dean! Blow me already!" Sam had never been more glad that they often lived out in the middle of nowhere because he was practically shrieking in frustration.

Suddenly his legs had dropped back down and Dean's hands, oh fuck, his rough warm hands, one was clasped wetly against Sam's cock and the other nestled right between his legs. Dean languidly licked Sam from base to tip, quietly reveling in the little shivers coasting down his brother's spine.

When he reached the top though he paused, letting a few warm breaths skate across the ruddy tip of Sam's dick. Another whine and Sam was up on his elbows, staring down at him with a mixture of blown out lust and annoyance. Perfect. Dean allowed himself one more teasing smirk and then, eyes still locked on his brother's, pulled as much of Sam into his mouth as he could. Sam's eyes rolled back into his head as the tip of his cock nudged the back of Dean's throat and he collapsed back onto the hood of the Impala.

Dean was pleasantly surprised by how much he could still take, even though it was years since he'd last blown someone. And no one he'd sucked off had ever been as big at Sam, although it wasn't as though that was a surprise, the kid was a giant after all. Still, as his lips skated up and down his brother's length, he wouldn't have had it any other way. The more of Sammy the better, he thought at this point.

Keeping Sam distracted while he reached for the glove and the lube wasn't particularly difficult either, the kid was arching into his mouth and not so much gasping for air as growling for it. All that stilled pretty quickly though as the first lubed up, latex covered finger pressed urgently around Sam's hole. As though they had suddenly been plunged into deep water, everything stilled and every sound quieted. Sam was still breathing heavily, but now it was silent, anticipatory, and slightly anxious. Dean was obviously experienced in this but, shit, Dean was the only guy Sam had ever wanted to...what if it...?

"Relax, Sammy," Dean purred and Sam, eager to please, tried to obey.

Little by little, with Dean still sucking away like a champ on his cock, Sam relaxed enough for two fingers to push through. Everything was boiling, his body felt too too hot, Dean's fingers bringing a constant flux of vulnerable pain and wanton need. But this was Dean, this was what he'd dreamed about, a thousand and one wanks since he was barely old enough to get hard, hiding under cheap motel sheets as they shlepped across the country over and over. If he was going to do this, it was fucking well going to be with Dean and it was gonna be now, since he had no idea whether he'd get another chance.

"Please, Dean, come on," Sam choked out as Dean slid in another (_God what were they on, three now?)_ finger.

"Get one of the condoms out for me, will ya?" Dean panted, letting Sam's cock slide wet out of his mouth. Sam scrambled to do as he asked, afraid he was going to rip the condom itself in two as he shucked it from it's wrapper. Dean's fingers receded slowly one after the other until Sam heard the snap of the glove coming off and the quick unzipping of Dean's jeans. God, he'd left Dean hanging all this time, he thought suddenly. _What if he's not even...?_

Any worries that Dean wouldn't be ready himself vanished as Sam felt the hot push of his brother's cock at his entrance. Dean's hands were once again grabbing Sam's hips like he thought his younger brother might get up and run at any minute as he pressed slowly, inch by inch in. They both stilled, shuddering ever so slightly, when Dean came to rest, wrapped up in his brother's heat.

Dean almost jumped when Sam reached out, suddenly, to grab his waist and pull himself in deeper. Sweet little noises were leaking from Sam's open mouth as he moved himself, unsure but needy up and down Dean's cock. It was really all the assurance Dean needed.

He grabbed Sam's hand and guided it to his leaking cock, then took over, pumping in and out slowly but surely. It wasn't a sight Dean ever thought he'd see, Sam spread out underneath him, moaning for him, begging for him. Years he'd thought about it, but spurned the idea just as coldly as he assumed Sam would him, if he ever knew. But Goddamn, here they were and it was all Dean could do to stop himself from coming immediately.

The Impala groaned under their combined weight as Dean fought to keep a steady rhythm, determined to make sure Sam came before he did. The prospect wasn't looking good however, if the tight coiling feeling in his stomach was anything to judge by. _Need to move things along, need to move things along now_, he thought desperately. With a harsh jerk, he lifted one of Sam's legs up over his shoulder again.

Sam was unprepared for the sudden rearranging of his body, leg muscles straining a little to accommodate their new position, but any complaints were short lived. He felt like he'd accidentally been electrocuted, jolts of lightning shooting up and down his spine as Dean's cock skimmed his prostate with very thrust. Before he could even see it coming, he felt his orgasm tearing through him, hard and fast and from the sound of it, Dean was hot on his trail, a nearly feral moan ripping through the air.

Neither one of them had bothered to move for a few minutes, each enjoying the warmth that was slowly seeping away from between them into the cold night air. When both Sam and Dean's breathing had returned to a somewhat normal pace and Dean was absolutely sure he wouldn't just fall the fuck over if he stood up, because that would be embarrassing has all hell, they quietly moved apart. A quick shuffle of clothes returning to their appropriate owner and place, then they were back to laying side by side on top of the Impala as though nothing untoward had happened at all.

But it certainly had. And Goddamn, wasn't Sam going to be a fucking coward about it and for once in his life, not push his luck. Because he'd actually done it, years of fucking thinking about it and now he'd gone and done it. Knowing Dean's repulsion for "chick-flick moments", Sam was pretty sure they'd never speak about tonight again. But at least he'd done it. And he'd got Dean to promise he wouldn't flip out about it tomorrow, well, not_ really_, but the implication had been there...

If Sam had had a drink he would have done a spit take when Dean spoke.

"So, if you want this to be a one time thing, comforting and all that," Dean said roughly, obviously trying to get what he wanted to say out as quickly as possible, "that's cool. Shit happens, I completely understand. But if you..." He broke off, clearing his throat awkwardly.

"If I what?" Sam could barely breathe, the nerves working his way up his belly, pushing savagely through the warm glow of sex.

"If you, you know...Goddamnit, Sammy." Sam heard Dean fill his lungs like he was going to start the underwater portion of the survival test Dad always put them through each summer. "If you'd want it to be a more regular thing, I'm down, I guess is what I'm trying to say."

The smile that moved over Sam's face felt wide enough to crack it in two. "Yeah," he said, still staring up at the stars, not daring to look over at his brother. "I'd like that."

Maybe, just maybe, things would turn out all right, they both though simultaneously. Maybe together, they could get through this.

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**Goodness! Well, if you enjoyed that or are looking for stories like it, feel free to check out my other stuff. Leave a constructive comment/whatever isn't screaming, if you feel so inclined! Ta for now, y'all!**


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